Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand

Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand
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DOI:
10.1021/ja0668825
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发表时间:
2006-12-27
影响因子:
15
通讯作者:
Kanemasa, Shuji
Kanemasa, Shuji
中科院分区:
化学1区
文献类型:
--
作者:
Ishimaru, Takehisa;Shibata, Norio;Kanemasa, Shuji

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描述了使用DBFOX−Zn(II)络合物的3-芳基和3-烷基-2-羟吲哚的第一个催化对映选择性羟基化反应,导致药学上重要的手性3-羟基-2-羟吲哚。氧化剂的结构对提高对映选择性起着重要作用。该方法已成功应用于使用DBFOX−Ni(II)配合物进行β-酮酯的高度对映选择性羟基化。
The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX−Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of β-keto esters using the DBFOX−Ni(II) complex.